GB576316A - Castor oil products and preparation of same - Google Patents
Castor oil products and preparation of sameInfo
- Publication number
- GB576316A GB576316A GB19644/43A GB1964443A GB576316A GB 576316 A GB576316 A GB 576316A GB 19644/43 A GB19644/43 A GB 19644/43A GB 1964443 A GB1964443 A GB 1964443A GB 576316 A GB576316 A GB 576316A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diallyl
- phthalate
- alcohol
- prepared
- allyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000004359 castor oil Substances 0.000 title abstract 5
- 235000019438 castor oil Nutrition 0.000 title abstract 5
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 title abstract 5
- 238000002360 preparation method Methods 0.000 title abstract 3
- -1 dimethallyl oxalate Chemical compound 0.000 abstract 10
- 239000002966 varnish Substances 0.000 abstract 8
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 abstract 5
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 239000003921 oil Substances 0.000 abstract 4
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 239000004641 Diallyl-phthalate Substances 0.000 abstract 3
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 abstract 3
- 229920000180 alkyd Polymers 0.000 abstract 3
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 abstract 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 abstract 3
- 230000018044 dehydration Effects 0.000 abstract 3
- 238000006297 dehydration reaction Methods 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 150000007519 polyprotic acids Polymers 0.000 abstract 3
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 abstract 3
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 abstract 2
- DSAYAFZWRDYBQY-UHFFFAOYSA-N 2,5-dimethylhexa-1,5-diene Chemical group CC(=C)CCC(C)=C DSAYAFZWRDYBQY-UHFFFAOYSA-N 0.000 abstract 2
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- 229910019142 PO4 Inorganic materials 0.000 abstract 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 2
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000010941 cobalt Substances 0.000 abstract 2
- 229910017052 cobalt Inorganic materials 0.000 abstract 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 2
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 abstract 2
- 235000010985 glycerol esters of wood rosin Nutrition 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 239000011133 lead Substances 0.000 abstract 2
- 229910052748 manganese Inorganic materials 0.000 abstract 2
- 239000011572 manganese Substances 0.000 abstract 2
- 125000005394 methallyl group Chemical group 0.000 abstract 2
- 239000005011 phenolic resin Substances 0.000 abstract 2
- 229920001568 phenolic resin Polymers 0.000 abstract 2
- 239000010452 phosphate Substances 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 2
- 239000000049 pigment Substances 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- RQNVJDSEWRGEQR-UHFFFAOYSA-N tris(prop-2-enyl) borate Chemical compound C=CCOB(OCC=C)OCC=C RQNVJDSEWRGEQR-UHFFFAOYSA-N 0.000 abstract 2
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 abstract 2
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 abstract 2
- PQMFVUNERGGBPG-UHFFFAOYSA-N (6-bromopyridin-2-yl)hydrazine Chemical class NNC1=CC=CC(Br)=N1 PQMFVUNERGGBPG-UHFFFAOYSA-N 0.000 abstract 1
- KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 abstract 1
- JPSKCQCQZUGWNM-UHFFFAOYSA-N 2,7-Oxepanedione Chemical compound O=C1CCCCC(=O)O1 JPSKCQCQZUGWNM-UHFFFAOYSA-N 0.000 abstract 1
- TWUZWTIVCCRAAD-UHFFFAOYSA-N 2-(2-butoxy-2-oxoethyl)-2-hydroxybutanedioic acid Chemical compound CCCCOC(=O)CC(O)(C(O)=O)CC(O)=O TWUZWTIVCCRAAD-UHFFFAOYSA-N 0.000 abstract 1
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 abstract 1
- CVMWVNOJZPCBTN-UHFFFAOYSA-N 6-oxo-6-(3-phenylprop-2-enoxy)hexanoic acid Chemical compound C(CCCCC(=O)O)(=O)OCC=CC1=CC=CC=C1 CVMWVNOJZPCBTN-UHFFFAOYSA-N 0.000 abstract 1
- 239000005995 Aluminium silicate Substances 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 229920001807 Urea-formaldehyde Polymers 0.000 abstract 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 abstract 1
- 235000012211 aluminium silicate Nutrition 0.000 abstract 1
- CIPHOUPBLAOEKY-UHFFFAOYSA-N azepane-1-carbodithioate;azepan-1-ium Chemical compound C1CCCNCC1.SC(=S)N1CCCCCC1 CIPHOUPBLAOEKY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000440 bentonite Substances 0.000 abstract 1
- 229910000278 bentonite Inorganic materials 0.000 abstract 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 abstract 1
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 abstract 1
- ZDNFTNPFYCKVTB-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,4-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C=C1 ZDNFTNPFYCKVTB-UHFFFAOYSA-N 0.000 abstract 1
- HABAXTXIECRCKH-UHFFFAOYSA-N bis(prop-2-enyl) butanedioate Chemical compound C=CCOC(=O)CCC(=O)OCC=C HABAXTXIECRCKH-UHFFFAOYSA-N 0.000 abstract 1
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 abstract 1
- FPODCVUTIPDRTE-UHFFFAOYSA-N bis(prop-2-enyl) hexanedioate Chemical compound C=CCOC(=O)CCCCC(=O)OCC=C FPODCVUTIPDRTE-UHFFFAOYSA-N 0.000 abstract 1
- BKXRKRANFLFTFU-UHFFFAOYSA-N bis(prop-2-enyl) oxalate Chemical compound C=CCOC(=O)C(=O)OCC=C BKXRKRANFLFTFU-UHFFFAOYSA-N 0.000 abstract 1
- 229910052810 boron oxide Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000008199 coating composition Substances 0.000 abstract 1
- 238000010411 cooking Methods 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- HANVTCGOAROXMV-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine;urea Chemical compound O=C.NC(N)=O.NC1=NC(N)=NC(N)=N1 HANVTCGOAROXMV-UHFFFAOYSA-N 0.000 abstract 1
- WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 abstract 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 abstract 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 abstract 1
- 125000005609 naphthenate group Chemical group 0.000 abstract 1
- 239000000025 natural resin Substances 0.000 abstract 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-M phthalate(1-) Chemical compound OC(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-M 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 abstract 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- PLCFYBDYBCOLSP-UHFFFAOYSA-N tris(prop-2-enyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound C=CCOC(=O)CC(O)(CC(=O)OCC=C)C(=O)OCC=C PLCFYBDYBCOLSP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F5/00—Obtaining drying-oils
- C09F5/06—Obtaining drying-oils by dehydration of hydroxylated fatty acids or oils
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A product suitable as a varnish oil is obtained by mixing castor oil with one or more polybasic acid esters of an unsaturated alcohol, which unsaturated alcohol contains an olefinic linkage between two carbon atoms, one of which is directly linked by a single bond to the carbinol group, and heating the mixture in the presence of a dehydration catalyst so that dehydration of the castor oil with simultaneous heat bodying of the mixture is effected. Suitable polybasic acid esters are diallyl carbonate, diallyl oxalate, dimethallyl oxalate, diallyl succinate, diallyl adipate, dimethallyl carbonate, dimethallyl succinate, dimethallyl adipate, diallyl phthalate, diallyl maleate, diallyl terephthalate, diallyl diglycollate, triallyl citrate, di-(b -chlorallyl) succinate, di - (b - chlorallyl) phthalate, di - (methylvinyl carbinyl) adipate, di-(methylvinyl-carbinyl) phthalate, dicrotyl mesaconate, dicrotyl phthalate, dicinnamyl glutarate, dicinnamyl phthalate, triallyl borate, triallyl phosphate, trimethallyl borate, tricinnamyl phosphate, allyl methallyl phthalate, allyl cinnamyl adipate, dimethallyl crotyl borate and diallyl monobutyl citrate. Dehydration catalysts include a number of metal sulphates, bentonite, p-toluene sulphonic acid, tungsten trioxide, phosphorus pentoxide, sulphuric acid, boron oxide, molybdenum oxide, kaolin, ammonium acid sulphate, phthalic anhydride and maleic anhydride. In examples: (a) castor oil is heated with diallyl phthalate in the presence of sodium bisulphate; (b) for comparison purposes, dehydrated castor oil is heated with diallyl phthalate; and (c) maleic alkyd varnishes and ester gum varnishes are prepared from the products of (a) and (b). Coating compositions may be prepared from the varnish oils by thinning with naphtha or aliphatic hydrocarbon thinners and adding such ingredients as lead, cobalt or manganese driers, pigments and plasticisers. Varnishes may be prepared from the varnish oils by cooking with natural or synthetic resins such as maleic or other alkyd resins (including rosin-modified alkyd resins), ester gum, phenolic resins, modified phenolic resins, rosin-modified ureaaldehyde resins, coumarone-indene resins, melamine-urea-formaldehyde resins, rosin and rosin derivatives like polymerized and partially hydrogenated rosin. The varnish compositions may contain stains, dyes, pigments, mineral thinners or other hydrocarbons, and driers such as lead, cobalt or manganese linoleates or the corresponding resinates or naphthenates or mixtures thereof. The unsaturated esters of polybasic acids used in the preparation of the varnish oils can be made in the usual manner from the appropriate alcohol. Specific preparation details, however, are given in some cases: (i) trimethallyl borate and tricinnamyl phosphate can be prepared by the methods described for triallyl borate and triallyl phosphate respectively in Beilstein's "Handbuch der organischen Chemie," Vol. I, page 439; (ii) allyl methallyl phthalate may be prepared by heating methallyl alcohol with phthalic anhydride to produce monomethallyl hydrogen phthalate and then esterifying with allyl alcohol in the presence of p-toluene sulphonic acid and benzene; (iii) allyl cinnamyl adipate may be prepared by forming monocinnamyl hydrogen adipate from cinnamyl alcohol and adipic anhydride and then esterifying it with allyl alcohol; (iv) diallyl monobutyl citrate may be prepared by forming monobutyl dihydrogen citrate from butyl alcohol and citric acid and then esterifying it with allyl alcohol; and (v) dimethallyl crotyl borate may be prepared by reacting together methallyl alcohol, crotyl alcohol and boric anhydride or acid. Specifications 547,854 and 576,317 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US576316XA | 1942-11-24 | 1942-11-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB576316A true GB576316A (en) | 1946-03-28 |
Family
ID=22011811
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB19644/43A Expired GB576316A (en) | 1942-11-24 | 1943-11-24 | Castor oil products and preparation of same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB576316A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113522323A (en) * | 2021-08-20 | 2021-10-22 | 南昌大学 | Eu-P-W composite catalyst and preparation method and application thereof |
-
1943
- 1943-11-24 GB GB19644/43A patent/GB576316A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113522323A (en) * | 2021-08-20 | 2021-10-22 | 南昌大学 | Eu-P-W composite catalyst and preparation method and application thereof |
CN113522323B (en) * | 2021-08-20 | 2022-06-24 | 南昌大学 | Eu-P-W composite catalyst and preparation method and application thereof |
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